Water → HCID 22063653, compound

HRID 1828536Notes

Reaction equation

HRID 1828536 reaction equation
[OH:1][C:2]1[N:3]=[C:4]2[CH:26]=[C:25]([CH2:27][CH2:28][C:29]3[S:30][CH:31]=[C:32]([CH:34]([CH3:36])[CH3:35])[N:33]=3)[CH:24]=[CH:23][N:5]2[C:6](=[O:22])[C:7]=1[C:8]1[N:9]=[N:10][N:11]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:12]=1.[CH2:37](N(CC)CC)C.S(OC)(OC)(=O)=O.O>CN(C)C=O>[CH:34]([C:32]1[N:33]=[C:29]([CH2:28][CH2:27][C:25]2[CH:24]=[CH:23][N:5]3[C:6](=[O:22])[C:7]([C:8]4[N:9]=[N:10][N:11]([CH2:13][C:14]5[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=5)[N:12]=4)=[C:2]([O:1][CH3:37])[N:3]=[C:4]3[CH:26]=2)[S:30][CH:31]=1)([CH3:36])[CH3:35]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl Sulfate2×HCID 8471TriethylamineHCID 135724437HCID 135724437, compound

Product 1

HCID 22063653HCID 22063653, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Hydroxy-8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-3-[2-(4-methoxybenzyl)-2H-1,2,3,4-tetrazol-5-yl]-4H-pyrido[1,2-a]pyrimidin-4-one (24 mg) was dissolved in dimethylformamide (1.5 ml), added with triethylamine (1.6 ml) and dimethyl sulfate (22 ml) and stirred overnight at room temperature. The reaction mixture was further added with dimethyl sulfate (5 ml), stirred for 4 hours, and then added with water and extracted with ethyl acetate. After the organic layer was dried over sodium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the title compound (5 mg).

Workup

  1. stirringstirred for 4 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialAfter the organic layer was dried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c650624eee434bc6b42a2c85a131dd07
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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